(R)-Verapamil
AlkaPlorer ID: AK018757
Synonym: None
IUPAC Name: (2S)-2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
Structure
SMILES: COC1=CC=C(CCN(C)CCC[C@@](C#N)(C2=CC=C(OC)C(OC)=C2)C(C)C)C=C1OC
InChI: InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3/t27-/m0/s1
InChIKey: SGTNSNPWRIOYBX-MHZLTWQESA-N
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Piper nigrum | Piper | Piperaceae | Piperales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
Properties Information
Molecule Weight: 454.6110000000002
TPSA？: 63.95
MolLogP？: 5.093080000000005
Number of H-Donors: 0
Number of H-Acceptors: 6
RingCount: 2
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Bacillus anthracis | Anthrax lethal factor | Potency | 1258.9 | nM | None |
| Cavia porcellus | Cavia porcellus | EC30 | 0.0611 | ug ml-1 | 10.1021/jm00167a033 |
| Cavia porcellus | Cavia porcellus | EC30 | 0.0694 | ug ml-1 | 10.1021/jm00167a033 |
| Homo sapiens | Arachidonate 15-lipoxygenase, type II | Potency | 12589.3 | nM | None |
| Homo sapiens | Arachidonate 15-lipoxygenase, type II | Potency | 15848.9 | nM | None |
| Homo sapiens | Ataxin-2 | Potency | 2818.4 | nM | None |
| Homo sapiens | Cytochrome P450 1A2 | AC50 | 15848.93 | nM | None |
| Homo sapiens | Cytochrome P450 1A2 | AC50 | 19952.62 | nM | None |
| Homo sapiens | Cytochrome P450 1A2 | AC50 | nan | None | None |
| Homo sapiens | Cytochrome P450 2C19 | AC50 | nan | None | None |
| Homo sapiens | Cytochrome P450 2C19 | Potency | 39810.7 | nM | None |
| Homo sapiens | Cytochrome P450 2C9 | AC50 | nan | None | None |
| Homo sapiens | Cytochrome P450 2C9 | Potency | 12.6 | nM | None |
| Homo sapiens | Cytochrome P450 2D6 | AC50 | nan | None | None |
| Homo sapiens | Cytochrome P450 3A4 | AC50 | 2511.89 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | AC50 | 3162.28 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | Ki | 1390.0 | nM | 10.2174/138920005774330639 |
| Homo sapiens | Cytochrome P450 3A4 | Ki | 2970.0 | nM | 10.2174/138920005774330639 |
| Homo sapiens | Cytochrome P450 3A4 | Kinact | 0.13 | min-1 | 10.2174/138920005774330639 |
| Homo sapiens | Cytochrome P450 3A4 | Kinact | 0.64 | min-1 | 10.2174/138920005774330639 |
| Homo sapiens | Cytochrome P450 3A4 | Potency | 2511.9 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | Potency | 3162.3 | nM | None |
| Homo sapiens | Homo sapiens | F | 13.5 | % | 10.1016/j.bmc.2007.08.060 |
| Homo sapiens | MAP kinase ERK2 | Potency | 15848.9 | nM | None |
| Homo sapiens | Multidrug resistance-associated protein 1 | Activity | nan | None | 10.1074/jbc.m703964200 |
| Homo sapiens | Multidrug resistance-associated protein 1 | Kd | 113.0 | nM | 10.1074/jbc.m703964200 |
| Homo sapiens | P-glycoprotein 1 | IC50 | 2090.0 | nM | 10.1021/jm020941h |
| Homo sapiens | P-glycoprotein 1 | IC50 | 2440.0 | nM | 10.1097/00001813-200302000-00012 |
| Homo sapiens | P-glycoprotein 1 | IC50 | 5330.0 | nM | 10.1097/00001813-200302000-00012 |
| Homo sapiens | Thyroid stimulating hormone receptor | Potency | 7943.3 | nM | None |
| Homo sapiens | Thyroid stimulating hormone receptor | Potency | 12589.3 | nM | None |
| Homo sapiens | Thyroid stimulating hormone receptor | Potency | 25118.9 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 26608.6 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 33498.3 | nM | None |
| Homo sapiens | Ubiquitin carboxyl-terminal hydrolase 1 | Potency | 28183.8 | nM | None |
| Mesocricetus auratus | BHK-21 | Activity | nan | None | 10.1074/jbc.m703964200 |
| Oryctolagus cuniculus | Oryctolagus cuniculus | EC30 | 0.0284 | ug ml-1 | 10.1021/jm00167a033 |
| Rattus norvegicus | Muscarinic acetylcholine receptor M1 | Potency | 12589.3 | nM | None |
| Rattus norvegicus | Muscarinic acetylcholine receptor M1 | Potency | 15848.9 | nM | None |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Activity | nan | None | 10.1038/s41586-020-2286-9 |
| None | ADMET | permeability | 5.62 | 10'-4 cm/s | 10.1021/jm901846t |
| None | ADMET | Ratio | 0.323 | None | 10.1124/dmd.110.035642 |
| None | NON-PROTEIN TARGET | Ratio | 0.409 | None | 10.1021/jm00167a033 |
| None | NON-PROTEIN TARGET | Ratio | 0.88 | None | 10.1021/jm00167a033 |
| None | Unchecked | Potency | 8912.5 | nM | None |
| None | Unchecked | Potency | 10000.0 | nM | None |
| None | Unchecked | Potency | 18356.4 | nM | None |
| None | Unchecked | Potency | 25118.9 | nM | None |